Palladium-catalyzed regio- and stereoselective allylic alkylation of 5-vinyloxazolidine-2,4-diones with azlactones: synthesis of chiral (Z)-trisubstituted allylic amino acid derivatives

Abstract

A palladium-catalyzed asymmetric decarboxylative allylation of azlactones with 5-vinyloxazolidine-2,4-diones as allylpalladium precursors is developed, which provides facile access to diverse (Z)-trisubstituted unnatural allylic amino acid derivatives in high yields with excellent enantioselectivities, exclusive Z-selectivities and regioselectivities towards linear products. Significantly, this method was proved to be workable in the scale-up synthesis of (Z)-trisubstituted chiral unnatural allylic amino acid derivatives, which were further transformed into ring-opening products while retaining the enantioselectivity and geometric control.